Annie's Anal Addition Ch. 02

As I got to know Karen she opened up even more on the twisted relationship she had with her husband. Of course people might’ve thought my developing sexual relationship with her was pretty twisted as well, the routine we developed where I would put her through the paces, really getting rough with her. Just the way she liked to dominate her husband, and work her rugged moves on him, so she loved it when I made her my plaything. And the main attraction had become me strapping on her big dildo and fucking her savagely, cunt and ass and both, just the way she strapped it on for her husband, and screwed the shit out of him.

With him turning over so happily for a solid fucking with a thick dildo, I asked her whether she ever thought about bringing a guy over to do her husband. But she said she could never even bring that up. Her husband may have loved to turn over and take it, but another guy, that was strictly taboo. This, of course, made me think of Tim.

I had even mentioned to her how I'd love it if I could watch her do her husband that way -- I'd never done it to a man like that myself then, really strap one on and play the stud --- and maybe have a turn at him too, but Karen said her husband would nix that idea too. He couldn't bear to put himself in that position with a woman other than his wife. Then Karen confessed that one thing she had really wanted to try was to dress up like a guy, then sort of 'pretend' that this 'guy' would shove her husband down to his knees and viciously fuck him. But she said he wouldn't have any part of that either. He wanted to be dominated only by a woman, by his wife -- a woman with a big dick. He'd tolerate her calling him a faggot worm and stuff like that when she fucked him, but that was about it. Looking Karen over I could see how her little fantasy of doing her self up as a guy would work too. She had really short hair, no tits and these narrow hips. She'd make a very convincing young stud, done up the right way.

Now I had done my thing with Tim and told Karen all about it, how I had busted Tim's asshole with my dildo, the way she liked busting her husband's.

"Shit, Annie. That makes me feel really hot, you telling me how you did that to this guy," she said, her eyes blazing with lustful curiosity.

"Tell me, Karen?" I asked her. "If these guys love having their butts eaten and fingered and fucked so much, how come they're so straight? That's what I can't figure out."

"Who knows? They don't want anyone to think they're fags, I guess."

"Too bad," I said, "Like wouldn't it really be far out to watch Tim and your husband get it on with each other."

"I don't know about that. This Tim sounds like quite a stud. I'd like to see him mix it up with another stud, not that wimp of a husband of mine."

"Yeah, I know what you mean. That would be so incredibly hot!" I said.

Then, suddenly, I had this bright idea.

"Hey, maybe you could do yourself up like a dude for Tim?" I told her. "He might go for something like that? I could ask him. Plus, he's been begging me to let him watch me make it with another chick and see if we could have her join us."

Karen's eyes lit up.

"Wow! That would be pretty cool!" she said, "I'd love getting into that with you, Annie. He sounds like such a stud, too" "Good," I said, all charged up. "I'll ask Tim and see what he thinks."

When I asked Tim, he was a little reluctant at first. Of course he craved the idea of another babe joining us, but when I told him that this babe would be a 'guy,' that she'd dress and look like one and that he'd have to pretend she was one, he was wary. But, eventually, I managed to persuade him, again telling Tim just how much all that would turn me on. Plus, when it came down to it, Tim had this strong kinky streak and once I brought up anything real twisted to him, I knew his curiosity would be piqued. And then again, he knew perfectly well that however much Karen might look and act like a guy, made up the way I planned to make her up, she was still a woman.

So I I told Karen that Tim was willing and she was absolutely thrilled. We decided on a weekday morning when her kids would be off to school and her husband would be at work. And planned to meet with Tim at his place. Karen loved the idea, that she, a thirty-three year old mother would be going over to this twenty-one year old stud’s place, dressed up as a young guy, for some secret and very twisted sex. We couldn't wait for the day!

And on that appointed day I went to pick up Karen. She asked me to come early so that I could help prepare her dress up as a guy, to strap it on and take care of all the details.

"I'm so excited," she said, her eyes sparkling with lust. "I can't wait!"

So now we went into her bedroom to get her ready for the role she was going to play, the role of a horny, boyish male stud about to seduce another dude!

First, I messed up her short hair a little so that it looked even more like she had a guy's haircut. A guy's usually going to be more casual about his hair than a woman. Then I reminded her to remove her wedding ring and a gold bracelet she was wearing.

A couple of weeks earlier Karen had told me she decided to let the hair grow under her arms. She had been to Europe last summer, and visited a nude beach. Karen said most women there still didn't shave under their arms, and she said she found that sexy and wanted to try growing it back herself. Of course that only helped the fantasy, Karen now having little tufts of hair under her arms.

Then she went to get her strap-on dildo. I remember how when she first mentioned it to me she said it was labeled the 'nine inch model,' I had used it on her plenty, but now looking at it, it seemed even bigger. But I had a feeling Tim would be able to handle it. He had instantly become a slut for a taking it up his ass. And of course we'd make sure we were liberal with the lubricant, and that would help.

"I'm always amazed at how real it looks," I said, handling it. Karen had told me that this one, like the one I had brought, was supposed to be molded from a real guy's erect cock. Except this guy was obviously considerably more hung that the dude who modeled for the dildo I had gotten!

Now she took off all her clothes and strapped the dildo to herself, as she had done many times before, I knew, for her husband. The dildo came complete with a set of life-like rubber balls.

"Shit, look at you!" I said, staring at her, naked, her huge cock sticking straight out from her very slender, boyish body. She gave me a nasty smile, standing there like a proud stud, fisting it with her hand.

"I'm hung, huh?" she said, showing it off.

"You sure as shit are!"

"Got a T-shirt?" I asked her as she fetched one from a drawer. "You should put it on to cover your tits."

"What tits?" she joked. "They may be small, but they're still tits, a woman's tits, so you've got to cover them up," I told her as she put on the T-shirt. With her husband she didn't bother with any of this. In fact, with him, she said she sometimes wore a garter belt and hose and high heels, trying to look ultra-feminine, when she strapped on her rubber cock. But then again, her husband wanted her femininity to be highlighted when she fucked him. He sought to be fucked by a woman, and the more womanly the better.

But with Tim it was going to be very different. This was going to be our fantasy, mine and Karen's, and for us the thing was that I, a babe, was going to bring over a 'hung, horny dude' to share with my boyfriend.

Earlier that day I went out and bought a small-sized pair of men's cotton briefs and now handed them to Karen.

"Here you go."

She slid them on and all of a sudden the transformation seemed almost complete. In her briefs and T-shirt she looked like a slim young guy, a guy who happened to have a raging hardon whose obscenely thick bulge was clearly visible under his briefs.

Then I had her put on a pair of jeans and some crew sock and tennis shoes. Karen liked to dress like this anyway, real casual and like a guy.

"How do I look?" she asked, staring at herself in the mirror, admiring the bulge in the crotch of her jeans.

"You look like a horny young dude," I said.

"I am a horny young dude," she said, rubbing her hardon, getting into the fantasy right away.

The other thing that was perfect about Karen for a scene like this was that she actually had a very low, rather gruff voice. So, on top of everything else, she almost sounded like a guy too.

"Oh man!" she said, thrilled. "I have a feeling this is going to be such a trip!"

"And what's your name going to be? It can't very well be Karen?" I asked.

"Oh, how about... how about Karl. That’s a guy’s name.”

"Karl... perfect!" I said, reaching down to squeeze the hunk of rubber bulging under the crotch of Karen's jeans. "I see you got a nice, big dick down here, Karl."

"Yeah," Karen hissed. "And I sure am aching to use it."

With that bulge obscenely visible to anyone who happened to look down, I reminded Karen to put on a raincoat so that it was covered when we went out. Tim lived in a high-rise with lots of tenants.

"That's why you need to wear the raincoat," I said, as I helped her on with it.

A half hour later we were at Tim's door, ringing the bell.

He let us in and immediately his eyes went wide when he took in what Karen looked like. I don't think he expected her to be quite that convincing. But, in fact, right now she looked exactly like a guy, a young smooth-skinned cute dude with an angelic face.

"Hi there," Karen said in her convincingly deep voice. Tim was also a little taken aback by that. "Tim... Karl," I said, introducing them.

"Can I get your coat?" Tim asked and Karen took it off. Immediately his eyes went wide again as he noticed that shockingly obvious bulge under the frayed denim of Karen's jeans.

I noticed Tim staring down at it, of course, and winked at him, which only made him blush.

Karen too, I could see, was a little nervous, so I'd have to be the mistress of ceremonies over here to start things off

"I was telling Karl all about you, Tim, and he got so excited that he had a hardon all the way coming over here," I said, brushing my hand over the bulge, over the rough fabric of the denim.

"And when Karl gets a hardon, he gets a hardon!" I teased. " 'Cause this dude is hung!"

Now I started squeezing Tim's crotch through his jeans, turning to Karen.

"Tim's never made it with a dude before, Karl," I said. "Can you believe that?"

"Well, we're going to have to do something about that, then," Karen said, looking straight at Tim now, gaining courage.

"He's a virgin with guys!" I said.

"I love good-looking virgin men," Karen said, moving closer, reaching down to squeeze Tim's crotch as I pulled my hand away. He may've been shocked into stunned silence still, but his cock had quickly begun to swell as I fondled him. Now I could see it swell some more as Karen took over.

Then I took hold of Tim's hand and placed it right on Karen's bulge.

"Yeah, why don't you two guys feel each other up while I get comfortable," I said, slowly taking off my clothes, knowing what effect that always had on both Tim and Karen, watching them squeeze one another's bulges.

Now I unbuckled Karen's jeans and pulled them down over her briefs. That cock was so huge that an inch or two of it stuck up out of those briefs. Karen's cock looked so incredibly real down to every detail that anyone could be fooled looking at it.

And Tim sure was looking at it. He was fixated on it, his eyes glued to it like a pair of lasers.

"It's something else, huh?" I said, pulling off Karen's briefs. Her T-shirt was long enough so that it covered the dildo strap. The effect was perfect. The only thing you could see now were 'Karl's' cock and balls, and they looked absolutely real.

"Now let's show Karl what you've got for him down there," I said, unbuckling Tim and pulling his jeans off along with his shorts.

His dick was still soft, though swollen, which was unusual for Tim. Normally his cock became erect the second he sensed sex was on the horizon. But no doubt he was probably still nervous about this scene.

"Here, let me get between you two studs," I said, having them sit on either side of me, then reaching over to take a cock in each hand, stroking them. Karen's, naturally, was its expected thick, hard nine inches, and now I could feel Tim's swelling and hardening in my hand.

"Mmmmh, two sexy studs," I purred. "I'm one lucky slut, aren't I?"

This whole scene really turned me on. For some time now I'd had fantasies of making it with two guys at once. It's just that the opportunity hadn't come along yet. Guys, I've found, are usually uptight about another dude sharing a chick, wondering whether they'd measure up. Plus, what I really wanted was a scene exactly like this one, where the two dudes not only paid attention to me, but paid attention to each other too. Now, with Karen playing the part of a guy, this fantasy was sort of half-coming through. I guess after it was over, I'd be only half a virgin when it came to having sex with two guys at once!

I stood up and moved away from them.

"Now I want to see you two studs handle each others' cocks," I told them, "Go on, fist each other!"

Karen eagerly reached over for Tim's cock, which was just about at full mast now. Tim was a little more hesitant.

"Come on, Tim,"I prodded. "Take it in your hand."

So now he reached over and took it in his hand. I loved the sight. Karen looked so much like a young guy, I was almost beginning to think of her as 'Karl' myself.

"Yeah, dude, manhandle that dick of mine while I manhandle yours," she said in her deep voice. "Let's show Annie over here how we do our guy thing. Let's get down and dirty for her. A couple of hot queers doing our cock thing, stud."

Beautiful! Karen got right in the groove, as I knew she would. Tim, though, blushed deeply when he heard Karen say that, use the word 'queer' to describe him.

"That's it, you queers!" I hissed. "Fist those cocks!"

Now Karen turned to Tim, looking him in the eye.

"How about I suck your dick, dude?" she asked and Tim nodded eagerly as she lowered her face to it and took it between her lips. She was really turned on, I could see. After all, this was a real treat for her, being normally limited to that shrimp dick of her husband's. And Tim carried almost as much down there as Karen's own thick nine inches!

"Now how about you give me some head?" she said, coming up for air as Tim looked at Karen, then at me.

"See, Karen," I said to her. "Like I said, Tim's never sucked a dude's cock before. He's a virgin when it comes to cocksucking and all that stuff. He says he's straight, but I know different. I know he wants to try it."

Hearing this only made Tim blush again, and Karen smile knowingly. Now she wrapped a hand around Tim's neck and pushed his head down to her lap, forcing him to mouth 'his' dick.

"That true, Tim? You never sucked cock before?"

He said nothing.

"Well, you sure as shit are sucking some now!" she cackled as she fed it to him.

"Yeah, look at you, Tim," I said, unable to keep from mercilessly teasing him. "You look like you'd make a great queer." Now I decided to join them again, kneeling on the floor and bringing both cocks to my face, pressing them together.

"Yum, yum," I purred. "Two big, juicy cocks. Let me have a taste."

I licked them both, then went back and forth, sucking one, then the other. I even tried to take both knobs in my mouth at once but I couldn't stretch my lips wide enough.

"Okay, dudes, now turn around," I said, getting them to kneel up on the bed and bend over, exposing both their two butts. Tim's, of course, was in plain view. But I had to discreetly slide over Karen's dildo strap to gain access to hers. Once I did that she looked just like a guy again, especially with those big, life-like balls staring me in the face.

"I know how much you faggots like this kind of action," I said, digging my tongue into Tim's crack, then Karen's, licking both their asses.

It was Karen who was always begging to eat my asshole, so it was quite a treat for her now, having me getting behind her, licking hers.

"How about you chew on this stud's ass now, Tim," I said, dragging him down behind Karen. I managed to camouflage the dildo strap as best as I could, covering it with Karen's T-shirt. Now Tim was staring at an asshole which could've been a guy's. And below that, a big set of rubber balls and a nine-inch rubber cock.

"Yeah, Tim, let me see you lick Karl's ass, lick it while I fist his big cock," I said, pushing Tim's face between 'Karl's' cheeks.

He lapped away at the morsel greedily.

"That's it, lick that faggot ass," I hissed.

I could hardly believe what I was doing. Here I was playing kinky, obscene games with an equally kinky stud, and a depraved, sex-crazed babe, a mother of two!

"Hey Karl?" I said to Karen. "How about you fuck me now and we let Tim watch."

Then I turned to Tim.

"Would you like that, Tim? Would you like to see Karl bury that huge dick of his in my cunt? Then later on he can bury it up your ass!" I said, licking my lips lewdly, gazing at Tim now with lust-crazed eyes.

"Yeah-- yeah, sure, I'd like to see that," Tim said, still a little stunned by everything that was happening.

So now I lay flat on my back and spread my legs wide, wagging a finger at Karen.

"Come down here, Karl, come down to my pussy," I purred, pointing to it as Karen got between my legs, trembling with excitement. Every other time it had been me fucking her, that was what she always sought and what she had gotten accustomed to. But now that Karen was 'Karl', a guy, she could get to do different things to me; she could get to fuck me! I knew that though she normally wished to be passive, that she loved the novelty of this. And so did I! And then of course, later on, she'd get to fuck something else, she'd get to fuck a man’s ass! And Tim, a stud who always boasted he was straight and nothing but straight, was going to take nine thick hard inches of cock all the way up his horny bottom!

"Oh yeah, slam it in there!" I shrieked, wrapping my arms around her body, pressing her to me, as she reached down to work her cock in my cunt.

Then I turned to Tim.

"Like watching another dude fuck me?" I asked.

"Uh huh!" he panted, though I wondered whether he'd feel that way if Karen were a real guy.

"Bring that thing of yours up here and let me suck it, okay? Let me taste that cock while Karl over here socks it to my pussy."

Tim knelt by my face and fed it to me. I loved it, every second of it! A big rubber cock deep in my cunt, a real one between my lips, what more could a horny young slut ask for!

"Now I want you to fuck me, Tim," I said, giving Karen the signal to pull out. I stayed where I was as Tim now got between my open legs and slammed his cock all the way inside me, feeling just as nice and stiff as Karen's.

Karen knelt by Tim's face, waving 'his' cock.

"Look at it," she said to him, "It's all slick and creamy from Annie's sopping cunt, so now why don't you suck it again and taste your girlfriend."

This time, while screwing me with a nice, hard, steady rhythm, Tim was more enthusiastic, taking Karen's cock in his mouth, wolfing it down.